Grilled Pineapple Upside-Down Cake

I’ve been eating a lot of pineapple lately, both fresh and canned. While I prefer the
taste of fresh pineapple, I appreciate the convenience of the pineapple rounds from
the can. This pineapple upside-down cake recipe uses fresh pineapple rounds,
although you can easily swap this out with canned pineapple.

I use fresh pineapple here, mostly because I’ve found that it holds up much better
on the grill, when you grill it with the core intact.

Grilled Pineapple Upside-Down Cake

I’ve been eating a lot of pineapple lately, both fresh and canned. While I prefer thetaste of fresh pineapple, I appreciate the convenience of the pineapple rounds fromthe can. This pineapple upside-down cake recipe uses fresh pineapple rounds,although you can easily swap this out with canned pineapple.
I use fresh pineapple here, mostly because I’ve found that it holds up much betteron the grill, when you grill it with the core intact.

Ingredients

  • 8 fresh pineapple slices (core still attached (the pineapple core is removed after grilling))
  • 2 tsp vegetable oil (for greasing your casserole dish)
  • 5 Tbsp salted butter (melted)
  • ½ cup + 1 Tbsp brown sugar
  • 8 maraschino cherries (drained and patted dry with paper towels)
  • 1.75 cups cake flour
  • 1.5 tsp baking powder
  • 1 tsp baking soda
  • 1 tsp Kosher salt
  • 7 Tbsp salted butter (softened)
  • ¾ cup white granulated sugar
  • 2 whole eggs
  • ½ cup sour cream
  • ¼ cup vegetable oil
  • 1 tsp vanilla extract
  • ¼ cup whole milk

Instructions 

  • Preheat your grill to 500F.
  • Clean grill grates with a grill brush.
  • Cut the rind off your pineapple, and cut 8 rounds from the pineapple
  • *The core will be included at this stage of the process, which helps the pineapple rounds stay together when grilled.
  • Grill the pineapple on each side, until you get nice grill marks on both sides.
  • When the pineapple is grilled, transfer to a cutting board and use a paring knife or
  • a small metal ring mold to cut the core out from each pineapple round.
  • Preheat the oven to 350F (180C).
  • Grease the bottom and sides of a casserole dish lightly with vegetable oil.
  • Melt the salted butter, and mix the melted salted butter in a bowl with the brown sugar.
  • Pour the butter and sugar mixture into the bottom of the lightly-greased casserole dish.
  • Place the grilled pineapple rounds over the surface of the melted butter and brown sugar layer.
  • Place the maraschino cherries inside the center of each pineapple round.
  • In a medium-sized mixing bowl, combine the cake flour, baking powder, baking
  • soda, and Kosher salt, and whisk to evenly distribute the dry ingredients.
  • In a large mixing bowl, mix together the softened butter and white granulated
  • sugar until they are a uniform consistency.
  • *You can use a stand mixer here if that is easier for you. In baking lingo, this is
  • called “creaming your butter and sugar together”.
  • Whisk in the 2 whole eggs until they are evenly mixed.
  • Whisk in the sour cream, vanilla extract, and whole milk until the wet mixture is homogenous.
  • Add the dry ingredients into the wet ingredients, and mix well. This is your cake batter.
  • Pour the cake batter over the grilled pineapple base you placed in the casserole dish earlier.
  • Bake at 350F (180C) for about 45-50 minutes, topping with aluminum foil halfway
  • through if the cake starts to take on too much color.
  • The cake is done when a toothpick inserted into the center of the cake comes out clean.
  • Remove the cake from the oven, and allow it to cool at room temperature for roughly 30 minutes.
  • Carefully use a paring knife to make sure the sides of the cake aren’t stuck to the sides of the casserole dish.
  • When the cake has mostly cooled, invert the cake carefully onto a serving tray, so
  • that the grilled pineapple slices and maraschino cherries are now on top.
  • Cut the cake into slices, and serve.

Notes

If you are using canned pineapple rounds instead of fresh pineapple, be carefully when flipping on the grill, as the canned pineapple rounds have a tendency to fall apart. Also, make sure your grill grates are hot, and well oiled.
If you are looking for something else to do with canned pineapple, try using it in a homemade pineapple pico de gallo, mixed with tomatoes, jalapenos, diced red onion, cilantro, and lime juice!
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